Your (US-centric) problem is introducing a subjective word 'fair' into
rules which humans have to apply (I am even willing to concede here that
lawyers are human).

What contitutes fairness? - exactly equal gliders and instruments (and
crew, etc, but you are not borrowing my wife), now that's fair. Or not,
depending on how you argue it.

In UK the siuation in question is simple. The gate opens, not at the
CD's whim, but with max height at 3,000ft AGL it opens 10 minutes after
the last glider in the class starts to be towed. For every 200ft added to
max height, add 1 minute. No ifs, no buts. The only thing the CD can do
after that is cancel the task and have a rebrief before the gate opens if
it is UNSAFE to continue.

Nobody pretended that gliding was fair when I was a boy in the Nationals.
The winner was the pilot with most points after the last day, however it
panned out.